ChemTeam Lab: Building Molecular Models of Simple Covalent Molecules

Before asking your teacher questions about how to do the lab, please read carefully, twice, the
entire "Day One" document.

Special Note: I will deduct 10% off your grade for playing with the model sets; as in "Look Mr.
ChemTeam, at this weird structure I made" or if I see you making a structure not in the assignment.
On the second occurrence, I will zero your grade.

Objective

1) Using a model building kit, construct models of a variety of simple covalent molecules.

2) Draw Lewis structures and/or structural formulas of selected models.

3) Draw all the isomers of selected formulas.

Brief Overview

In 1874, J. H. van 't Hoff (1901 Nobel Prize in Chemistry) was the first to suggest that molecules have
a three-dimensional structure. He used this idea to explain several previously puzzling facts about
chemical compounds.

In this lab, we will use a kit to model the 3D structure of a number of molecules, including several
that van 't Hoff focused on. After building the molecular models, you will draw them on paper in a
manner intended to represent the 3D appearence. You will also draw Lewis structures for some of
the molecules as well as isomeric structures for those formulas that have them.

Safety

The parts of the kits are not toys. Use them only as instructed and only for the purposes of the lab.

Equipment List

One molecular model kit

Procedure
Part I. Preliminary Steps

1) Examine the front cover of the model building kit. At the bottom, it tells you the colors for each
element. When you open the kit, there is one main component missing. These are small, white
connectors which you will not be using. Also, there may be two shades of green for the chlorine
atoms. This has no chemical meaning. It is just that the kits were bought at different times and the
green pigment varied from lot to lot.

2) Examine the various atom models and note the number of holes in each. When you make a
model, you MUST fill up each hole with a bond. For example, black represents carbon and each
carbon sphere has four holes. To make correct structures, you MUST fill all four. There is one
exception to this. The pale blue atom (representing nitrogen) has four holes. Please use only three.
By the way, carbon is black and nitrogen is blue. Those of you who use a blue sphere for carbon have
made a mistake and, most likely, you made the mistake because you didn't read (and remember)
this particular section.

3) Examine the light gray connectors. The short, thick ones are to be used to show single bonds. The
longer, bendable ones are for double and triple bonds. You need to use two for double bonds and
three for triple bonds. Do not mix long and short connectors between bond types. In day four, there
will be a situation where you need to use the thinner connectors for single bonds.

4) Make the following molecules: H2, O2 and N2. These three demonstrate the use of single, double
and triple bonds. Please do not click the link until you have built the models.

A picture of these three models.

5a) Now, make H2O and NH3. Both of these molecules use only single bonds. Please do not click the
link until you have built the models.

A picture of these two models.

5b) Now, make CO2 and HCN. The first uses two double bonds and the second uses one triple bond
and one single bond. Please do not click the link until you have built the models.

A picture of these two models.

Data Table Comment: more than likely, many of you will start drawing structures of H2 and the
others just above. This is a mistake due, most likely, to your failure to read through the entire
document (and remember the important parts) before beginning work. Before starting to draw
structures, please make sure you review all the instructions below concerning how to make the data
table.

Part II. Experimental Steps

6) Following the list below, continue to build models. There are not enough atoms to build all the
molecules discussed below, so build some, then break them down, then build more.

a) Alkane (7 structural, 3 Lewis) is the category name for a set of compounds which contain carbon
and hydrogen and ONLY single bonds. An alkane has the general formula of CnH2n + 2. Build the
following alkanes:

Special Note: there are TWO (or more) different ways to make some structures, starting with the
C4H10 formula. Make only the structure where the carbons are connected in a line. Do not make
any structures that have the carbons branching. See the discussion below for more on this point.

b) Alkene (3 structural, 2 Lewis) is the category name for a set of compounds which contain carbon
and hydrogen, ONE double bond and the rest single bonds. An alkene has the general formula of
CnH2n. Build the following alkenes:

8. ethene (also called ethylene), C2H4 A picture of ethene

9. propene (also called propylene), C3H6 A picture of propene

10. butene (also called butylene), C4H8 A picture of butene

Special Note: Butene can have the double bond in two different locations. For your answer, please
use only the structure where the double bond is between the first and second carbons.

c) Alkyne (3 structural, 2 Lewis) is the category name for a set of compounds which contain carbon
and hydrogen, ONE triple bond and the rest single bonds. An alkyne has the general formula of
CnH2n - 2. Pronounce alkyne to rhyme with "nine." Build the following alkynes:

Special Note: Butyne can have the triple bond in two different locations. For your answer, please use
on the structure where the triple bond is between the first and second carbons.

Part III. Clean-up Steps

7) Unconnect all bonds from the atom models and replace in the box. Inspect around your table top
and on the floor for lost atoms or bonds.

8) With any remaining time in the class period,

Please read carefully all of the instructions below. Let's repeat that: please read carefully all of the
instructions below. Also, please do this BEFORE you come up to the teacher, asking questions about
what to do.

Data Table Instructions: The above data table should cover all 13 of the assigned substances in Part
II, Experimental Steps, above (13 structural, 7 Lewis). (You need not draw any structures from Part I,
Preliminary Steps.) The first column of the data table need only be wide enough for the molecular
formula. I recommend against making the three columns each 1/3 of the paper.

1) There should be only one structural formula for each molecular formula. Please use lines and
wedges as explained below.

2) Do Lewis structures as well for molecules with three or less carbons. Lewis structures use dots
only, no lines whatsoever. That means with 4 or more carbons, only show a structural drawing in
addition to the molecular formula. In other words, do not do Lewis structures for the compounds
with 4 or more carbons.

3) In your drawings, do not show any hydrogens on substances with 4 or more carbons, except for
the hydrogen on an -OH. This applies to answer the discussion question as well as to the data tables.

It is best to make a rough draft of the table first, then make a final draft. Students have a tendancy to
allow for too little space to draw structures, then they cram them into the too small space and then
say "Whaaaaat?" when the teacher deducts points. Your shock and outrage at being so treated will
not deter me in my professional judgment of your data table.

Please draw your structural formulas in the same style as the CH4 is done. The meaning of the three
kinds of bond symbols in the above data table example:

1) the solid wedge bond means the hydrogen is coming out of the plane of the paper.

2) the dashed line (sometimes a wedge) bond means the bond is going away from you, behind the
plane of the paper.

3) the solid line bond means the bond is in the plane of the paper.

Always have as many atoms as possible in the plane of the paper. For example, C2H2 can have all 4
atoms in the plane, as if you were above the molecule, looking down. C2H4 can have all 6 atoms in
the plane. Once again, maximize the number of atoms in the plane.
By the way, the plane you should use to put atoms in is the one in front of you and parallel to you.
Do not select a plant that would intersect your body. In other words, one at an angle (like 90° or
perpendicular) to your body.

Also, the carbon atoms should be oriented left to right. For example, consider a four-carbon chain.
Hold the molecule so the atoms from a sawtooth pattern running left and right, as opposed to the
four carbon atoms being viewed up and down. Another way to say it: the carbon atoms should be
viewed "spread out" as opposed to "on top of each other."

In your drawing, try to approximate the angles between atoms, as revealed in the model you've
made. Once again, in C2H2, you would draw the hydrogens at 120° to the placement of the double
bond.

As much as possible, make all the carbons in a chain to be co-planar, with only hydrogens (or
chlorine or whatever) going behind or in front of the plane. In addition, make one hydrogen on each
terminal carbon be co-planar with the carbon chain. When oxygen or nitrogen is involved, try to
make them co-planar to the carbons.

Special Data Table Notes: (1) Do not draw bonds in the curved manner as seen in the picture of the
O2 molecule. Draw the double bond (and triple bond) using straight lines only. (2) Do not draw the
element symbols with circles around them. Do not draw only circles to represent atoms. What you
should draw are the letters of the elements, as in the CH4 structure in the data table example.

Discussion

Structural Isomerism

The general definition of isomer is: two (or more) different chemical substances that have the same
molecular formula. The key point is that the substances are DIFFERENT chemicals, but have the same
number of each kind of atom.

There are a number of different ways to make isomers; the simplest of which is to have different
connectivity. Connectivity refers to how the atoms (carbon, nitrogen, oxygen, hydrogen, etc.) in a
molecule are connected to one another.
For example, consider the formula C4H10. There are TWO ways to connect the four carbons. Can
you figure them out before looking at the picture?
By the way, there are only two. Make the top structure in the picture, again if necessary, and then
twist it to some other arrangement. Maybe like the one to the right? Is it a different substance than
the top one in the other picture? If you say yes, what's to stop me from just twisting it right back to
the original way? You cannot bend and twist a molecule to get a different connectivity. You must
remove one (or more) carbons and put them SOMEWHERE ELSE (than from where they were
removed) in the molecule.

Here's your discussion assignment: draw all the isomers for C5H12 (there are three), C6H14 (there
are five), and C7H16 (there are nine). Want more? NOOOOOOOOOOO!!!! cries the poor, befuddled
chemistry student!! OK, but if you did want more, there are 18 isomers of the formula C8H18, but
you don't have to do them, just the C-4, C-5, C-6, and C-7.

There is no fast and easy way to construct possible isomers. The only way is through trial-and-error.
However, do not be too quick to judge that you have, say, the nine isomers of C7H16. If one
structure can be bent or twisted to exactly overlap with another, then the two models are of the
same substance.

There is, however, a systematic way to approach the trial-and-error. First, make the straight chain
molecule, as you did above for the data table. Now, remove ONE carbon and move it to a different
location. After you've exhausted the possibilities, then move TWO carbons. However, keep in mind
that it gets a bit more complex. Two carbons can be moved as two one-carbon fragments or one
two-carbon fragment. Keep on exhausting all the possibilities.

However, one warning: if you get more isomers than I did, who do you think stands the better
chance of being wrong?

Do not do them in the data table format above. I suggest a title like "The nine isomers of C7H16" and
then the structures neatly done on the page.

Do not draw the C-4, C-5, C-6, C-7 isomers using wedge and dashed bonds. Draw them flat, using
only solid lines for bonds. You do not need to draw them in a sawtooth pattern, as the C-4 example
is done in the data table.